| | DIELDRIN Basic information |
| Product Name: | DIELDRIN | | Synonyms: | Dieldrin Solution in Methanol;Dieldrinsolution,100ppm;1,2,3,4,10,10-HEXACHLORO-1,4,4A,5,6,7,8,8A-OCTAHYDRO-6,7-EPOXY-1,4:5,8-DIMETHANONAPHTHALENE;2,7:3,6-Dimethanonaphth[2,3-b]oxirene,3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-,(1aR,2R,2aS,3S,6R,6aR,7S,7aS)-rel-;Dieldrin Solution in Methanol solution, 100ppm;Dieldrin, Pesticide Mix;1,2,3,4,10,10-HEXACHLORO-6,7-EPOXY-1,4,4A,5,6,7,8,8A,-OCTAHYDRO-1,4,-ENDO-5,8-EXO-DIMETHANONAPHTHALENE;1,2,3,4,10,10-HEXACHLORO-6,7-EPOXY-1,4,4A,5,6,7,8,8A-OCTAHYDRO-ENDO,EXO-1,4:5,8-DIMETHANONAPHTHALENE | | CAS: | 60-57-1 | | MF: | C12H8Cl6O | | MW: | 380.91 | | EINECS: | 200-484-5 | | Product Categories: | Agro-Products;Heterocycles;Analytical Chemistry;PesticidesMethod Specific;2000/60/EC;Pesticides;Chlorinated Compounds (Environmental Endocrine Disruptors);Environmental Endocrine Disruptors;2000/60/ECMore...Close...;Alpha sort;Baby Food Directives 13/2003 EC&14/2003 ECPesticides;CyclodienesPesticides&Metabolites;D;DAlphabetic;DID - DINMethod Specific;European Community: ISO and DIN;Insecticides;Method Specific;Oeko-Tex Standard 100 | | Mol File: | 60-57-1.mol |  |
| | DIELDRIN Chemical Properties |
| Melting point | 143-144 °C(lit.) | | Boiling point | 496.11°C (rough estimate) | | density | 1.75 g/cm3 | | vapor density | 13.2 (vs air) | | vapor pressure | 30.7 and 58.5 at 20 and 25 °C, respectively (gas saturation-GC, Grayson and Fosbraey, 1982) | | refractive index | 1.5550 (estimate) | | Fp | 2 °C | | storage temp. | APPROX 4°C
| | solubility | Soluble in ethanol and benzene (Weast, 1986) | | form | neat | | Water Solubility | 195ug/L(25 ºC) | | Merck | 3103 | | BRN | 91396 | | Henry's Law Constant | 27.6 at 5 °C, 63.2 at 15 °C, 82.9 at 20 °C, 97.7 at 25 °C, 217 at 35 °C:in 3% NaCl solution: 66.1
at 5 °C, 158 at 15 °C, 395 at 25 °C, 507 at 35 °C (gas stripping-GC, Cetin et al., 2006) | | Exposure limits | NIOSH REL: TWA 0.25 mg/m3, IDLH 50 mg/m3; OSHA PEL: TWA 0.25 mg/m3; ACGIH TLV: TWA 0.25 mg/m3. | | Stability: | Stable. Breakdown product of aldrin in the environment. Incompatible with acids, active metals and strong oxidizing agents. | | IARC | 2A (Vol. 5, Sup 7, 117) 2019 | | EPA Substance Registry System | Dieldrin (60-57-1) |
| | DIELDRIN Usage And Synthesis |
| Chemical Properties | white or light brown powder or crystals | | Chemical Properties | Dieldrin is a colorless to light tan solid with
a mild chemical odor. The Odor Threshold in water is
0.04 mg/L | | Physical properties | White crystals to pale tan flakes with an odorless to mild chemical odor. Odor threshold
concentration is 41 μg/L (quoted, Keith and Walters, 1992). | | Uses | Dieldrin was first used by cotton growers in the 1950s; it has
subsequently been used on other crops for the control of
vectorborne diseases and for mothproofing woolen goods.
Dieldrin, as well as other cyclodiene insecticides, is uniquely
suited for the control of termites. In 1974, the U.S. registration
of products containing aldrin and dieldrin was canceled.
As a result of worldwide concerns regarding the potential
human health and environmental impacts of dieldrin, its
manufacture ceased by the early 1990s.
Occupational exposures have occurred among all groups
that have been involved in the manufacture or handling of the
compound, and in the spraying of dieldrin suspensions and
emulsions. Overexposure, resulting in acute intoxication,
occurred primarily in the early days of dieldrin, aldrin,
and endrin manufacture and in spraying operations with
these compounds in Kenya, India, Iran, and other malariainfested
countries. | | Uses | Stereoisomer of Endrin. Used as an insecticide.
Potential occupational carcinogen.
| | Uses | Formerly as insecticide. | | Definition | ChEBI: Dieldrin is an organochlorine compound resulting from the epoxidation of the double bond of aldrin. It is the active metabolite of the proinsecticde aldrin. It has a role as a xenobiotic and a carcinogenic agent. It is an organochlorine insecticide, an organochlorine compound and an epoxide. It is functionally related to an aldrin. | | General Description | DIELDRIN is a light-tan flaked solid. DIELDRIN is insoluble in water. DIELDRIN is toxic by inhalation, skin absorption and ingestion. DIELDRIN can penetrate intact skin. DIELDRIN is used as an insecticide. | | Air & Water Reactions | Insoluble in water. | | Reactivity Profile | DIELDRIN is sensitive to mineral acids, acid catalysts, acid oxidizing agents and active metals. DIELDRIN reacts with phenols. DIELDRIN is also slightly corrosive to metals. DIELDRIN may react vigorously with strong oxidizers such as chlorine and permanganates and strong acids such as sulfuric or nitric. | | Health Hazard | Inhalation, ingestion, or skin contact causes irritability, convulsions and/or coma, nausea, vomiting, headache, fainting, tremors. Contact with eyes causes irritation. | | Health Hazard | Highly toxic; toxic symptoms similar to theseof aldrin; affects central nervous system,liver, kidneys, and skin; causes headache,dizziness, nausea, vomiting, tremor, ataxia,clonic and tonic convulsions, and respiratoryfailure; oral LD50 value (mice): 38 mg/kg;causes liver cancers in animals; inadequateevidence in humans; RCRA Waste Number P037.
Exposure to many organochlorine pesticides has been linked to an increasedrisk of Parkinson’s disease. In this context,dieldrin has been the most implicated ofall. Dieldrin has been found, during postmortem, in the brain tissues of humanswith Parkinson’s disease, indicating that itpromotes dopaminergic degeneration. Various neurotoxic studies following exposure todieldrin have been conducted in both cellcultures and animal models. Such studiesindicated that dieldrin-induced neurotoxicity via mechanisms associated with dopaminergic degeneration including oxidative stress,mitochondrial dysfunction, protein aggregation, and apoptosis. Such effects cancause neuronal cell death and neurodegenerative diseases including Parkinson’s disease.Kanthasamy et al. (2005) have revieweddieldrin-induced neurotoxicity.. | | Fire Hazard | Special Hazards of Combustion Products: Toxic and irritating hydrogen chloride fumes may form in fire. | | Agricultural Uses | Insecticide: Manufacture in the United States prohibited since
1974. In 1987, EPA banned all uses. Banned for use in
EU (also for export) All uses of dieldrin (and Aldrin) were
canceled in 1974, except for subsurface ground insertion
for termite control, dipping of non-food roots and tops,
and moth-proofing by manufacturing processes in a closed
system (EPA 1974). In 1987, these final three uses were
voluntarily canceled by the sole manufacturer. Currently
there are more than 25 global suppliers | | Trade name | ALVIT®; BELCO®[C]; COMPOUND
497®; D-31®; DIELDREX®; DIELDRITE®;
ILLOXOL®; KILLGERM DETHLAC INSECTICIDAL
LAQUER®; OCTALOX®; OXRALOX®; PANORAM®;
PANORAM D-31®; PRENTOX®[C]; QUINTOX®;
ROYAL BRAND®[C]; SD 3417® | | Safety Profile | A human poison by
ingestion and possibly other routes. Poison
experimentally by inhalation, ingestion, skin
contact, intravenous, and intraperitoneal
routes. Experimental teratogenic and
reproductive data. Absorbed readily through
the skin and by other routes. It is a central
nervous system stimulant. Questionable
carcinogen with experimental carcinogenic,
neoplastigenic, and tumorigenic data.
Human mutation data reported. An
insecticide. Dieldrin is considerably more
toxic than DDT by ingestion and skin
contact. Dieldrin or its derivatives may
accumulate in the body from chronic low
dosages. When heated to decomposition it
emits toxic fumes of Cl-. See also ALDRIN. | | Potential Exposure | Aldrin belongs to the group of cyclodiene insecticides. They are a subgroup of the chlorinated
cyclic hydrocarbon insecticides which include DDT, BHC,
etc. They were manufactured in the United States by Shell
Chemical Co. until the United States Environmental
Protection Agency prohibited their manufacture in 1974
under the Federal Insecticide, Fungicide, and Rodenticide
Act. The primary use of the chemicals in the past was for
control of corn pests, although they were also used by the
citrus industry.
Dieldrin’s persistence in the environment is due to its
extremely low volatility (i.e., a vapor pressure of
1.78 3 1027 mmHg @ 20°C), and low solubility in water
(186 μg/L @ 25°C29°C). In addition, dieldrin is
extremely apolar, resulting in a high affinity for fat which
accounts for its retention in animal fats, plant waxes; andother such organic matter in the environment. The fat
solubility of dieldrin results in the progressive accumulation in the food chain which may result in a concentration
in an organism which would exceed the lethal limit for
a consumer. | | Carcinogenicity | Accumulating evidence suggests that
dieldrin is “not a likely human carcinogen”
and that it acts as a species-specific hepatocarcinogen
in mice through nongenotoxic
mechanisms.
The 2003 ACGIH threshold limit valuetime-
weighted average (TLV-TWA) for dieldrin
is 0.25mg/m3 with a notation for skin
absorption. | | Environmental Fate | Biological. Identified metabolites of dieldrin from solution cultures containing Pseudomonas sp. in soils include aldrin and dihydroxydihydroaldrin. Other unidentified byproducts included a ketone, an aldehyde and an acid (Matsumura et al., 1968; Kearney and Kaufman, 1976). A pure culture of the marine alga, namely Dunaliella sp., degraded dieldrin to photodieldrin and an unknown metabolite at yields of 8.5 and 3.2%, respectively.
Photodieldrin and the diol were also identified as metabolites in field-collected samples of marine water, sediments and associated biological materials (Patil et al., 1972). At least 10 different types of bacteria comprising a mixed anaerobic population
Chacko et al. (1966) reported that cultures of six actinomycetes (Norcardia sp., Streptomyces albus, Streptomyces antibioticus, Streptomyces auerofaciens, Streptomyces cinnamoneus, Streptomyces viridochromogenes) and 8 fungi had no effect on the degradati
The percentage of dieldrin remaining in a Congaree sandy loam soil after 7 years was 50% (Nash and Woolson, 1967). Soil. Dieldrin is very persistent in soil under both aerobic and anaerobic conditions (Castro and Yoshida, 1971; Sanborn and Yu, 1973). Reported half-lives in soil ranged from 175 days to 3 years (Howard et al., 1991).75 days to 3 years (Howard et al., 1991). Groundwater. According to the U.S. EPA (1986) dieldrin has a high potential to leach to groundwater.
Photolytic. Photolysis of an aqueous solution by sunlight for 3 months resulted in a 70% yield of photodieldrin (Henderson and Crosby, 1968). A solid ?lm of dieldrin exposed to sunlight for 2 months resulted in a 25% yield of photodieldrin (Benso | | Shipping | UN2761 Organochlorine pesticides, solid, toxic,
Hazard Class: 6.1; Labels: 6.1-Poisonous materials. | | Toxicity evaluation | Consistent with its intended use on insects in soil, dieldrin is
not very water soluble. However, dieldrin readily binds to
sediment, but rarely leaches into deeper soil layers and
groundwater. It takes decades to break down in the environment, and past agricultural uses of dieldrin have
resulted in persisting soil residues and uptake in a wide range of
crops.
The half-life of dieldrin in temperate soils is approximately
5 years, while it degrades faster (up to 90% in 1 month) from
tropical soils.
Dieldrin may be volatilized from sediment and redistributed
by air currents, contaminating areas far from their sources.
Nationally, levels of dieldrin have declined since agricultural
uses were discontinued.
Dieldrin readily bioaccumulates in terrestrial and aquatic
organisms. Biomagnification factors ranging from 2.2 (in
rainbow trout) to 16 (in herring gulls) have been reported for
dieldrin. Bioconcentration factors for dieldrin in various
aquatic organisms range from 400 to 68 000, indicating that
dieldrin shows moderate to significant bioaccumulation in
various aquatic species. | | Incompatibilities | Incompatible with strong acids: concentrated mineral acids; acid catalysts; phenols, strong oxidizers, active metals; like sodium, potassium, magnesium,
and zinc. Keep away from copper, iron, and their salts.
| | Waste Disposal | Incineration (816C,
0.5 second minimum for primary combustion; 1760C,
1.0 second for secondary combustion) with adequate
scrubbing and ash disposal facilities. In accordance
with 40CFR165, follow recommendations for the disposal
of pesticides and pesticide containers. Must be disposed
properly by following package label directions or by
contacting your local or federal environmental control
agency, or by contacting your regional EPA office.
Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste
containing this contaminant (≧100 kg/mo) must conform
with EPA regulations governing storage, transportation,
treatment, and waste disposal |
| | DIELDRIN Preparation Products And Raw materials |
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